Hydrochloric Acid → HCID 9849572, compound

HRID 1070109Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:14]\[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:19][CH:18]=2)/[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.Cl>O1CCCC1.CO.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:14]\[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[O:28][C:29]=3[CH3:30])=[CH:19][CH:18]=2)/[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Ethyl E-2-(4-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (600 mg) was dissolved in tetrahydrofuran (6 ml)-methanol (3 ml), and 1N aqueous solution of sodium hydroxide (3 ml) was added and the mixture was stirred for 1 hour at 40° C. 1N HCl (3.3 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystals were recrystallized from ethyl acetate to obtain E-2-(4-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetic acid (516 mg, yield 99%) as colorless crystals. m.p. 159-160° C. (decomposition)

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residual crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-ee61440daada45c5969db0f45e560537
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251926B1

Reaction notes

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